Water → 2-(4-cyano-1H-indol-1-yl)acetamide

HRID 2244617Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]#[N:13])[C:6]=2[CH:5]=[CH:4]1.Br[CH2:15][C:16]([NH2:18])=[O:17].O>CN(C=O)C>[C:12]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]2[CH2:15][C:16]([NH2:18])=[O:17])#[N:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 60% NaH (12.38 g) in DMF (480 ml) was added a solution of 1H-indole-4-carbonitrile (40.0 g) in DMF (80 ml) at 0° C. After stirring at 0° C. for 30 min, it was stirred at room temperature for 0.5 hour. Thereafter, a solution of 2-bromoacetamide (40.76 g) in DMF (80 ml) was added dropwise thereto at 0° C. The solution was warmed from 0° C. to room temperature, and stirred for 12 hours. To the reaction solution was added water (1200 ml), and the precipitated white solid was collected by filtration. The solution was washed with hot water (300 ml) and diisopropyl ether (200 ml) to obtain 2-(4-cyano-1H-indol-1-yl)acetamide (52.1 g) as a white solid.

Workup

stirringit was stirred at room temperature for 0.5 hour
customat 0° C
temperatureThe solution was warmed from 0° C. to room temperature
stirringstirred for 12 hours
filtrationthe precipitated white solid was collected by filtration
washThe solution was washed with hot water (300 ml) and diisopropyl ether (200 ml)

Sources & evidence

ORD record: ord-82952c39a4914455bcf899912530df1c
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678820B2

Reaction notes

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